Need help getting along with partners, relatives, coworkers... and people in general? Ask Prudence! Emily Yoffe -- a.k.a. Slate's advice columnist Dear Prudence, was online Tuesday, June 23 to take your questions on manners, morals and more.

Bowie, Md.: Dear Prudie, I have a great boyfriend of 2 years, and there are no major problems between us, except that he rarely brushes his teeth. When I can see the plaque on his teeth, I usually end up pulling away when he kisses me. The other thing about it is that if I can see the plaque others can, too. How can I gently tell him to pick up a tooth brush?

Emily Yoffe: For two years you have been watching the Great Wall of Plaque build on your boyfriend's teeth and you can't think of a way to tell Mr. Gingivitis he's repulsing you? I'd say that's a major problem. Forget gentle hints. Tell him it's not a moral issue that keeps you from kissing him, but an oral one. Say he needs to visit a dentist immediately and start regularly brushing and flossing or else your commitment to him is going to be as loose as his teeth.

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St. Louis, Mo.: My best friend got diagnosed with Stage 4 Melanoma. She talked to me about how she wished she had gotten pregnant before she got sick, and now the doctors are telling her she has to wait at least 3 years before she can try to conceive, due to chemotherapy and radiation. We are both in our mid 20s, and while I got married before her and have a young son, her situation made me want to get pregnant. I had been waiting to have a second kid until time was "right" which it never has been, due to school, work, husband's unemployment and so on. I decided no time was perfect, and now I'm eight weeks along. I don't know how to tell my best friend without hurting her. I know she will be more hurt if I don't tell her soon.

Emily Yoffe: What you don't do is tell her that her struggle with mortality has prompted you to have another child. You're right, since you are best friends and this is something you would have told her if she hadn't become ill, you do have to let her know. Surely, not all your conversations revolve around her illness, and when you're talking about normal things, you should simply tell her, "I have some exciting news -- I'm pregnant." Be sensitive to her response. Sure, she might burst into tears and say she fears this will never happen for her. To which you say that you long for the day when she has a child of her own, you are so sorry that she has to endure this ordeal, and you admire the way she is facing it. Be understanding -- not defensive -- about her pain. And don't get backed into a corner having to explain why you chose this time. What you said here is right -- life rarely offers perfect opportunities.

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London, Ontario: I'm from Southern Ontario, where weddings involve a minimum of 3 events for female guests: a shower, a phenomenon that I believe is unique to the region called a stag-and-doe, where one is expected to purchase a ticket and drinks and to pay to play games, all to defray the costs of the wedding, and the big day itself. Each event involves an outlay of cash, of course, a minimum of $100 for all 3.

I've managed to avoid the circus for the past several years by living abroad, but now I'm back and getting ready to start grad school in September. Between now and then, I've been invited to 4 weddings, 4 showers and umpteen stag and does, which are not limited to guests. All of the couples already live together and have much nicer homes and incomes than I do.

I intend to go to the weddings, and have already purchased modest gifts for each. I have turned down the other events. In part, I don't have the money. But the larger part of my reluctance is my belief, which I keep to myself, that the wedding industry is out of control. However, I am facing a lot of questions as to why I'm not going to this or that stag and doe or shower. Can you suggest a good, neutral response that doesn't sound old the 12th time?

Emily Yoffe: I often wonder where the idea that your friends are supposed to defray the costs of your life events got started. I guess we should be grateful that it's mostly confined to weddings and we all don't get regular grocery bills or requests to help with the annual vacation from our married friends. The way to stop being part of this is to do what you're doing: just give something appropriate that you can afford. You don't have to have an original response as to why you aren't doing more. Just keep repeating, "Unfortunately, I can't make that event."

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Washington, D.C.: Dear Prudence, I have been dating my boyfriend for a little over a year now, and he is absolutely fantastic. Very attractive, very loving, very kind -- the list goes on and on. The issue (and of course there is one), is that he is a bit older than me -- I'm 28 and he's 45. Most of the time the age difference doesn't bother me, since we get along so well. However, when I think about the long-term, I worry about the issues that may arise, such as him dying well before me. Am I crazy to be dwelling on issues that are so far down the road (he is in excellent health), or should I seriously consider that our age difference may be too great a barrier to overcome?

Emily Yoffe: What's crazy is for people who are considering spending their lives together to not address the issues that are bound to come up, such as whether to have children, religious differences, etc. Sure, this age difference may not seem so dramatic now, but 17 years is a big gap and you have to think through the implications. That said, there is no guarantee that even a person closer to your age will live a long, healthy life. And many couples with big age differences have long, successful marriages. If you do want to spend your lives together, your age difference, and what it will mean to your work lives, reproductive lives, etc. is something you should feel open about talking about.

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Anonymous: Dear Prudence,

I am married to a wonderful man who is tolerant, patient, and kind. He's generous to me, and I adore him. The problem is my stepson, who still lives at home. The boy is 21 years old and has never held a job, had a driver's license, or done a voluntary chore around the house. He sits in front of his computer all day or sleeps. My husband doesn't seem inclined to make him get a job or support himself in any way. I know his reluctance has to do with guilt about their childhood (some mutterings of abuse by his ex). While my stepson isn't a bad kid (no drugs, drinking, etc.), I can't help but want him to move out start his own life and leave me and his father to ours. We've talked about this issue before, and it leaves us both unhappy. How can I nudge this bird from the nest?

Emily Yoffe: Your husband's guilt and indulgence, as it tends to, has crippled its recipient. There is obviously something wrong with your stepson -- despite a difficult childhood he lacks even the most basic human drives for independence and self-respect. Your family needs professional intervention. Your stepson needs a full medical and psychological work up to get to the bottom of why he's missed the basic milestones (friends, work) of becoming an adult. And you two need someone to help you figure out how to start giving your stepson the tools to fledge.

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Dayton, Ohio: Dear Prudie,

I'm a 33-year old professional man who has had very long hair since my teens. Men in my family have had long hair for generations. My friends and family don't even think about it -- it's normal. The problem is how to respond when a co-worker or random person says, "You ought to donate it."

First, I don't like people telling me what to do. Second, I had cancer when I was a child and don't like talking about it. If someone really wants to help, they should donate to Ronald McDonald House instead of telling me to cut my hair. Not every kid with cancer, like me, goes bald, but they do need toys and their families need support. Saying this only seems to embarrass folks and then I have to explain my whole life story. Been there, done that. Not interested. Third, I have cultural and religious reasons for not cutting my hair and don't feel the need to explain those, either.

How can I politely tell these folks to stop telling me what to do without guilt-tripping them and having to re-hash a difficult and very personal time in my life?

Emily Yoffe: I admire you for not saying, "And that's a nice watch -- you ought to donate it to Goodwill." What you do with your hair is none of anyone's business. It's up to you whether you want to tell people that you have religious reasons for keeping your hair as it is. But you don't even have to offer that. To strangers, you can simply walk away. To friends you can say, "That's not for me," and leave it at that.

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Anonymous: Dear Prudence, I recently found proof that my husband of 24 years has cheated on me with a secretary from work.

I confronted him with the evidence. At first he denied he knew anyone with that name. Then he tried to alter the evidence while I was out of the room.

Finally he admitted his infidelity.

He has never said he was sorry.

He has refused to seek therapy.

He refuses to answer any questions about the affair.

Do I owe him a "second chance"? I have always thought that an affair was something that a marriage should be able to weather. But I don't see how we can reestablish trust given his lack of remorse. Would I be justified to seek a divorce and move on with my life?

I want to be fair.

Emily Yoffe: If by second chance you mean his having another affair, then it sounds as if you're all set. It's hard to move into the "We're renewing our commitment to each other" stage if your husband seems only committed to continuing to cheat. Since at every opportunity he's taken the tack of compounding his deceit, he's left it up to you to decide to accept his behavior as it is. You, however, might want a good divorce attorney on your side in case your husband has plans for the marital assets that he's also not letting you in on.

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San Juan Islands, Wash.: About eight years ago, my husband and I decided to help two of his sisters -- both single mothers -- buy their own houses. We wrote up no official papers, had no formal date for being repaid. (Yes, I know now this was all a bad idea.) One of them paid us back several years ago. The other has never mentioned it. As I saw her become financially stable, her children grown and moved out of the house, I kept expecting her to bring up how she might begin to repay us. My husband refused to ask her about it, saying she'd bring it up when she was ready. After a couple of years of wondering, I finally wrote her a letter saying this uncomfortable matter was still between us and asking for us to talk about it. She responded by writing a letter only to my husband, saying she was surprised that the "private agreement" that existed between her and my husband of his "generous gift" might be causing him pain. My husband was angry that I had gone "behind his back" to write a letter to his sister. He says now that he has always hoped that one day she would "pay it forward" to another family member but that whatever she does is her own business. I feel like she --and he-- have cut me out of the discussion of what happens to our money($20,000!). What should I do?

Emily Yoffe: Yes, the original mistake was not clarifying the terms of the loan. Since enough time has gone by for your sister-in-laws children to have grown and left, even a low interest rate would be a nice return for you now. Your second mistake was taking action without your husband. This has backfired by making it his family against you. "Pay it forward" is a lovely idea, but it sounds as if your sister in-law just decided to stick with the "pay" portion of this aphorism and has no use for "forward" let alone paying it back. Given the high feelings, you should apologize to your husband and say you want to let the issue go for now. Then in a few months say to your husband you know you behaved inappropriately by writing to your sister-in-law, but you wanted to bring it up again with him to see if you both could get some recompense from his sister for your long ago and generous loan.

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Virginia: Hi Prudence, My husband of one year is in the military and was recently sent overseas for a two year stint. It is hard for both of us, but he especially is having a hard time. I am trying to be as supportive as I can for him. While clearing out his closet to make room for some of my clothes (he knew I was moving some of my stuff in), I came across a stash of pictures and letters he had saved from an ex-girlfriend. The pictures were mostly all sexy -- no nudity, but she's in a bikini in a lot of them. I did not look through the letters. I didn't want to make myself any more upset than I already was, and I didn't want to violate his privacy.

Anyway, my question is what do I do now? I don't want to make my husband's life any more stressful than it already is, but this is really bothering me. The sexiness of the pictures he saved is I think what upsets me most. He knows I have always been insecure about this ex. And he has had other girlfriends which he dated for much longer than her, but he only had pictures of this one girl. I don't know if I should say something so that we can try to work through it together or if I should keep quiet about it, since he really is going through a tough time right now. Thanks for your help!

Emily Yoffe: Put the pictures away and forget about them! Everyone is entitled to have a stash of memorabilia and his is pretty mild. You and your husband are physically separated and he's under duress. You need to be a loving supportive, presence for him now. Think of what he would do if you brought this up to him. He would reassure you that he forgot about the pictures, she means nothing to him now, and it's just some stuff he forgot to get rid of. But the conversation would leave you both feeling uncomfortable, especially at such a great distance. So pretend he's reassured you, remember he's chosen you, reseal the envelope and put it out of your sight and your mind.

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Embarrassed: My husband and I married over a year ago and were blessed with many generous gifts from our friends and family. I began the thank you notes when we returned from our honeymoon and then life happened. By "life" I mean we applied, were accepted to and started grad school, we held an intervention for his mother, assisted her enrollment in rehab, assisted her search when she escaped from rehab, attended family counseling sessions with her and now try to avoid her daily crises; cared for a grandparent in between nursing stays; helped a friend leave an abusive spouse, testified before family court and local law enforcement; and tried to celebrate some good times and holidays with friends and family. So now I have a thousand excuses and hundreds of thank you notes left.

Is it okay to send them this late? Do I have to explain why they are so late?

Emily Yoffe: I like the range of your excuses from mother-in-law's escape from rehab to, well, going on vacation. No, it's not too late to write the notes, and no, no one wants to hear that the reason they are coming this late is because granny got sick and you were at the beach working on your tan. Sit down and write the notes. Add a one-line apology for the long delay, but don't clarify the reasons.

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The Steamy South: Dear Prudie ,

I've recently decided I'm tired of people asking me if I'm expecting another baby/and decided to lose some weight. My mother, who has been complaining about her weight ever since I can remember, said that she was going to join me in my efforts. But every time I go to her house for dinner, she serves the same old things she always cooks -- mouth-watering ribeye steaks, creamy mashed potatoes, decadent desserts. Even the vegetables are smothered in butter before they reach the table.

My eating plan allows me to eat anything in moderation, but she always cooks enough for ten people and then pressures me to eat more than I should. If I refuse, she acts hurt. To make matters worse, she's an excellent cook, so I really want to eat what she's offering.

My parents split their time between the town where my brother lives and the town I live in. I've managed to lose 15 lbs since May in spite of my Mom's food pushing, but we're going to visit my brother and his family in 2 weeks. I already know I won't be reducing while I'm there, but I don't want to put on the pounds I've already lost. How do I deal with my mom's insistence that I eat more than I know I should?

Emily Yoffe: Once you're out of her house, and she no longer has the power to physically put a spoon in your mouth or punish you if you don't clean your plate, your mother cannot make you eat more than you want to. We live in a fortunate world where it's harder to avoid food than find it. You will always be surrounded by temptation, so you need to strengthen the ability to say, "It looks great, but I'm full, thanks" to your mother or whoever might be pushing calories on you. Take a look at The End of Overeating by David Kessler or The Beck Diet books for ideas on how to change how you interact with food.

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"Loan": The "lender" and the "giver" both have tax implications. This looks like a gift, so one needs to claim it as so and the other has to file a gift tax return. If a loan, it was still below market, and thus had a gift component. The IRS is not really happy with people who do this without filing, and they do come after you years later. See a CPA, stat.

Emily Yoffe: You mean you can't say to the IRS, "But what about 'paying it forward'?" Thanks for the information that "Loan" needs to bring this up with her husband.

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London, U.K.: We have several young children, all the same gender, and (surprise!) are suddenly expecting another. We haven't yet shared the good news, but it is inevitable that people will ask us if we were trying for that elusive other gender. We weren't. I don't want to tell the world this child was a surprise, and I don't want to be rude, tempting though it may be considering the question is so personal.

My honest answer is that I would prefer this child be the same as the others, but I don't think I should say that. The trite answer is that "we just want a healthy baby." How would you respond?

Emily Yoffe: There are good reasons that some situations already have a trite answer. This one is excellent, so use it.

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Washington, D.C.: Dear Prudie,

I'm a 27-year-old woman who's doing pretty well in life. I've traveled the world; I'm getting my Master's degree and have a great job lined up; I'm in perfect health and in great shape. People always tell me I'm really pretty, smart, fun, nice, and adventurous. I'm really happy with every aspect of my life except my love life.

I've tried meeting guys in all sorts of situations, such as in class, at work, through friends, at events, online, etc., and sometimes I'll get a few dates. Things tend to end with the guy offering me casual sex or nothing, and plainly telling me that he has no desire to have a relationship with me, and that's when I'm lucky, as I've had worse endings on numerous occasions. I'm left mindboggled and bitter, because I really want to be in a relationship.

I would think that being an attractive, accomplished person would make me good relationship material, but apparently that's just not enough. I know lots of people who are less nice, less funny, and less interesting who manage to find boyfriends. What can I do differently that will make guys think I'm girlfriend material?

Emily Yoffe: I've said before that I've often wished I could put together all the "attractive, smart, nice, accomplished" people who have somehow managed to get pretty far into adulthood without ever having a romantic relationship. You should start by asking your friends to have a blunt conversation with you as to why they think you've never connected with a guy. Is there something you're doing that they haven't wanted to mention to you? Beyond figuring out what signals you may be sending, you've got to work on not getting angry and bitter -- that would make any potential partner flee. Keep trying, keep open, keep your expectations low, and ask your friends to help you connect with men who have expressed a desire to have a serious girlfriend.

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Philadelphia, Penn.: Two good friends of mine have been dating for about six months. I cheered on the relationship in the beginning, but am now wishing I had completely butted out. Friend #1 is head over heels in love with Friend #2, and is currently planning a cross-country move to be with her. In our phone conversations, he tells me how great she is, how he's in love with her, etc. Friend #2 is clearly not as interested. When we talk on the phone, she'll just say he seems "cool" and "pretty nice", and how he's "probably good for her" after the jerks she's dated. (A fiancé broke up with her two years ago). I honestly think she wants to like him, but it's pretty obvious that the feelings aren't there. I know I should stay out of their business, but the thought of Friend #1 uprooting his life to move to the West Coast is heartbreaking -- especially since I'm pretty sure he wouldn't if he knew how lukewarmly she talked about him.

Emily Yoffe: This is your chance to completely butt out. They are both adults and it's up to Friends #1 and #2 to decide where they want to live and how they want to conduct their romantic lives.

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Philadelphia, Penn.: Hi Prudie, My husband and I just bought plane tickets to go see a friend's new baby in August. But my mother-in-law just informed me that she's having a big 60th birthday party for herself that weekend! She was really upset when she heard we'd be out of town, but changing the tickets will be hundreds of dollars. What should we do?

Emily Yoffe: You have to look at this in the longer term than the immediate cost. Is your mother-in-law's weekend absolutely set, or is she flexible? If it's set, you and your husband know if she's the kind of person who, after her initial upset, would say she understands she should have told your earlier, and she knows it will be too hard to change your travel plans, then you can go. But maybe she's the kind of person who will bring this up at her 70th, 80th, and 90th birthdays. If that's the case, amortize the cost of the tickets over those decades, and tell your friends you have to reschedule.

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Glendora, Calif.: Hi Emily.

I need a little workplace guidance. About once or twice a week, a male coworker will buy a coffee drink for myself and another female in the office. The gesture is very sweet and much appreciated. The problem is that neither I nor my female coworker like the drink he chooses for us. It feels like a waste of money for him to spend 3 or 4 dollars for each of us when we both inevitably pour the drinks down the drain.

What is the polite thing to do in this situation? Would it seem ungrateful to tell him what kind of drink I would prefer or should I just let him continue to spend his money in vain to spare his feelings?

Emily Yoffe: This guy is shelling out about $16 a week in unwanted gifts, so that's a lot of money to go down the drain. Also, picking up an occasional coffee, etc. for a colleague is one thing, but a constant stream of one-way gifts can be uncomfortable The two of you should tell him that while you very much appreciate his thoughtfulness, both of you are trying to cut down on snacks, and that the drinks are delicious but too caloric for you. Tell him that he's wonderfully generous, but your waistlines and his wallet would be in better shape if he cut back.

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Just overweight, thanks: Speaking of people asking if you're expecting a baby, is there way to say "no" that isn't awkward for them? It happened to me recently in a professional context, and I wasn't sure the best way to get past the moment.

Emily Yoffe: I think Dave Barry's rule is the best: Never ask a woman you're not sure is pregnant if she's pregnant even if you notice a baby's head appears to be emerging from her. Yes, this is embarrassing for all concerned. So if you're the one being asked, you can laugh it off by saying, "I'm not. But if I were the fathers would be Ben & Jerry."

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Emily Yoffe: Thanks everyone. Talk to you next Monday.

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